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MyTravelHacks: How to get 5 roundtrip tickets to Hawaii for $775

This article shows how to get 5 roundtrip tickets from the West Coast to Hawaii for $775, but it’s just an example. You could use the same strategy to fly almost anywhere in the U.S. (or abroad) many times for less than $1k.

The hack uses two of my favorite credit cards: The Alaska Visa Signature and the Chase Sapphire Preferred. If you have these cards already — great — you can use them for this hack. If you don’t: Please only get them if you’re paying off your current cards and your credit is good.

Now, down to brass tacks (whatever those are.)

The Alaska card provides three bonuses that we care about for the purposes of this hack:

A signup bonus of 40,000 Alaska miles (after minimum spend)

An companion fare, which lets someone else travel on the same itinerary for $121, no matter the cost of your original ticket

3x miles for each dollar spent on Alaska

The Chase card offers tons of things, only one of which we care about here:

A signup bonus of 60,000 Chase Ultimate Rewards Points

You’ll want to wait to apply for the second card until you’ve hit the minimum spend on the first card. Then you’ll have 60,000 Chase points, 40,000 Alaska miles, and a companion fare.

Here’s how to use them:

Tickets 1 + 2: Companion Fare

Assuming a roundtrip ticket to Hawaii costs about $450 (with a deal from MyTravelNerd, naturally), buying two tickets with the Alaska companion fare will be $450 + $121 = $571. These are the only tickets you’ll pay for with cash.

Bonus: You’ll earn ~5,000 Alaska miles for flying this route, and 1,713 miles for using your Alaska card to pay for the tickets. So you now have 46,713 Alaska miles in the bank.

Ticket 3: Alaska miles

Alaska offers one-way flights from the U.S. to Hawaii for as little as 15,000 miles, but 17,500 seems more common. Two one-ways will therefore cost you 35,000 miles, leaving ~12,000 Alaska miles for future use.

Tickets 4 + 5: Chase points -> Avios

Here’s where things get a little travel-hacky, but don’t worry, it’s not super complicated. Chase points can be transferred to a number of partners, including British Airways’ Avios program. You can book a flight on Alaska (using Avios) for as little as 12,500 each one-way.

Two roundtrip tickets will therefore set you back 12,500 x 4 Chase points, leaving 10,000 for future hacking.

Here’s a full breakdown, including the small fees in cash for each award ticket:

5 roundtrip flights would normally cost $2,250 (very conservatively) so this hack you saves about $1,475. Not bad.

Again, there are umpteen ways you could use these two cards to score cheap travel, this is just one (fairly) straightforward option. Have questions? Other great ideas for using these cards? Comment below and let me know!